Methanol → Ethyl 4-amino-2-(methylsulfonyl)-5-thiazolecarboxylate

HRID 1161546Notes

Reaction equation

HRID 1161546 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[S:10][C:9](SC)=[N:8][C:7]=1[NH2:13])=[O:5])[CH3:2].[CH3:14]O.O[O:17][S:18]([O-:20])=O.[K+]>O.C(OCC)(=O)C>[CH2:1]([O:3][C:4]([C:6]1[S:10][C:9]([S:18]([CH3:14])(=[O:20])=[O:17])=[N:8][C:7]=1[NH2:13])=[O:5])[CH3:2]

Participants

6

Reactant 3

HCID 887MethanolHCID 384908Ethyl 4-amino-2-(methylsulfanyl)-1,3-thiazole-5-carboxylateHCID 23707502Potassium hydroxy sulfite

Product 1

HCID 59516885Ethyl 4-amino-2-(methylsulfonyl)-5-thiazolecarboxylate

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

After adding 41.8 g of 4-amino-2-methylsulfanylthiazole-5-carboxylic acid ethyl ester [CAS No. 39736-29-3] to 3 liters of a water:methanol=1:1 mixed solvent at room temperature, 352 g of Oxone™ was added thereto in small portions over a period of 15 minutes with stirring. The mixture was stirred at room temperature for 16 hours and then poured into a mixture of 8 liters of ethyl acetate and 5 liters of water. The organic layer was washed with 5 liters of water and 3 liters of saturated brine and then dried over anhydrous magnesium sulfate. The desiccating agent was removed by filtration, and the filtrate was concentrated under reduced pressure to give the title compound (34.5 g) as a light yellow solid.

Workup

  1. stirringThe mixture was stirred at room temperature for 16 hours
  2. washThe organic layer was washed with 5 liters of water and 3 liters of saturated brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customThe desiccating agent was removed by filtration
  5. concentrationthe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-f7b04d77bd6b4bee9642f473b4dc7389
Source dataset
uspto-grants-2010_10
Patent number
US07816522B2

Reaction notes

Loading…